When comfort food and a traditional recipe collide it can only mean one thing: pineapple upside-down cake. This moist and dense cake with a sticky caramel topping was a dessert staple in the good old days but it’s so much better today with fresh pineapple and raspberries (for that bright red touch). Fresh fruit vs. canned takes an old-fashioned dessert to a new sophisticated level and this easy-to-follow recipe means you can make it any time.

Is that pineapple ripe? Want to know the secret to a ripe pineapple? Tug on the green leaves on top. If they pull out easily, you’ve got a ripe pineapple. My produce friend at Shoprite taught me that!

Raspberries vs. cherries: Sure it’s retro, but nuclear red maraschino cherries do not have to be the rule when making pineapple upside down cake. Raspberries in all their natural red beauty are an excellent substitute and they taste great too.

About cast iron skillets: Cast iron skillets literally last for generations and the older, the better. Don’t let the dark, heavy look turn you away. Cast iron is a reliable conductor of heat for optimal cooking. The more you use it, the more “seasoned” it gets creating a natural non-stick surface.

Pineapple Upside-Down Cake
This pineapple upside-down cake uses fresh fruit vs. canned taking an old-fashioned dessert to a new sophisticated level.

Pineapple Upside-Down Cake

Prep Time: 15 minutes

Cook Time: 40 minutes

Serving Size: 6-8


  • ½ cup (1 stick) unsalted butter, divided
  • ½ cup dark brown sugar
  • ½ ripe pineapple, peeled, cored and sliced in ½ -inch slices (5-6)
  • 10-12 fresh raspberries
  • ¾ cup sugar
  • 1 large egg
  • 1-teaspoon vanilla
  • 1 1/3 cup four
  • ¼ teaspoon salt
  • 2 teaspoons baking powder
  • ¾ cup milk


  1. Pre-heat oven to 350 degrees. Place ½ stick of butter in a 10-inch cast iron skillet and place in the pre-heating oven to melt. Remove from the heat and sprinkle the brown sugar on top. Arrange pineapple slices, so they make a circle. It’s okay if they overlap. Place 1-2 raspberries in the pineapple holes.
  2. In a large bowl with an electric mixer, beat remaining butter and sugar until light and fluffy. Beat in egg followed by vanilla. In another bowl whisk together flour, salt and baking powder. Slowly add to wet ingredients, then, mix in milk. Pour evenly on top of the pineapples and bake 35-40 minutes until set. Cool in pan for 5 minutes then gently flip the cake onto a serving platter.


Home cook’s note: If you don’t have a cast iron skillet, a regular 9-inch cake pan will do just fine.